Apatow was a writer and producer on such television shows as The Ben Stiller Show, Roseanne, The Critic, Freaks and Geeks and Undeclared; and such movies as Heavyweights, The Cable Guy, Anchorman: The Legend of Ron Burgundy, The 40-Year-Old Virgin, Talladega Nights: The Ballad of Ricky Bobby, Knocked Up, Superbad, Walk Hard: The Dewey Cox Story, You Don't Mess with the Zohan, Pineapple Express, Funny People, Bridesmaids and The Five-Year Engagement.

Apatow auditioned for Jim Henson's experimental television pilot Handmade Video along with friend Adam Sandler. Apatow did not get the part because Jim Henson said he "lacked warmth." Apatow and Sandler talked about the audition in a 2009 interview promoting their film Funny People.[1]

Adam Sandler:

Judd stole an audition away from me with Jim Henson.

Judd Apatow:

That's right. Jim Henson was doing a reality show, where you would drive around the country with your own video cameras.

Adam Sandler:

At that time, Judd said he didn't even want to be on camera anymore. Judd was slowly starting to say, "Maybe I just want to be a writer." I didn't even know what he was talking about. I was like, "What's a writer?" Then, we auditioned for Jim Henson and I was so cocky. I was like, "Oh, I can't wait for that callback." Then, Judd was like, "Yeah, they called. They were interested in me."

Judd Apatow:

But, I ultimately didn't get it because Jim Henson said I lacked warmth. When the guy who taught me how to read told me that I lacked warmth, I was devastated.